Escape to this serene Florida Keys retreat featuring multiple outdoor pools and a relaxing hot tub. Located just minutes from stunning beaches, enjoy convenient amenities like free WiFi and parking while exploring nearby Upper Sugarloaf Key attractions.
Dive into a tropical oasis at this Key West resort featuring a marina, poolside bar, and complimentary bicycles. Just minutes from Smathers Beach and Duval Street, guests love the 24-hour fitness center and helpful staff.
This garden hotel offers a relaxing escape with outdoor pool, jacuzzi, and poolside bar. Just minutes from Key West Airport with a free area shuttle to nearby attractions including Duval Street and Smathers Beach.
Escape to this beachside haven with 5 outdoor pools, umbrella-dotted shores, and full spa offering facials and massages. Just minutes from Sombrero Beach, enjoy two bars, a poolside lounge, and Mahina restaurant after a workout in the fitness center.
Soak up the sunshine at this Marathon beach hotel with cabanas and loungers. Just 10 minutes from Sombrero Beach, this resort offers 2 outdoor pools, a poolside bar, and The Bistro serving American cuisine. The full-service spa provides rejuvenating treatments.
This beachfront resort offers a full-service spa for ultimate relaxation after sun-filled days. Enjoy cuisine at El Farito, one of 4 restaurants, or drinks at multiple bars while marina views unfold. Just a short drive from Sombrero Beach and local art galleries.
Experience Florida Keys laid-back charm at this waterfront hotel with a marina and outdoor pool. Grab seafood at Porky's Bayside restaurant, explore Marathon on complimentary bikes, or drive just minutes to Sombrero Beach's soft sands.
Feel the coastal breeze at this Big Pine Key marina resort where adventure awaits. Hike scenic trails, kayak crystal waters, or lounge by the pool. Near Blue Hole and Bahia Honda State Park, with rooms featuring microwaves and free WiFi.
Escape to this Marathon aparthotel featuring an outdoor pool and apartments with premium bedding. Located within a 15-minute drive of Sombrero Beach and Vaca Key, guests enjoy free WiFi and parking. The helpful staff and clean rooms earn top marks.
Experience oceanfront bliss at this peaceful retreat with stunning sunset views. Just a 5-minute drive from Smathers Beach and Florida Keys Beaches, enjoy the outdoor pool, poolside bar, and complimentary breakfast before exploring nearby Duval Street with the convenient shuttle service.
Escape to this Marathon sanctuary with a private beach where loungers await by crystal waters. Just minutes from Sombrero Beach, enjoy 3 outdoor pools, rejuvenating spa treatments, and local cuisine at TJs Tiki Bar as the sun dips below the horizon.
Breezy oceanfront getaway offering a refreshing pool and 24-hour fitness center. Just minutes from Duval Street and water activities like scuba diving. Enjoy restaurant dining and bar service with easy access to Key West's famous beaches.
Immerse in tropical living at this family-friendly resort near Duval Street and Smathers Beach. Enjoy 2 restaurants including the Toasted Coconut serving American cuisine, plus 2 poolside bars, a hot tub, and 24-hour fitness center, all with free WiFi.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Escape the tourist rush at Cutthroat Harbor Estates, a peaceful slice of paradise on Summerland Key. This residential waterfront neighborhood offers crystal-clear waters perfect for fishing, kayaking, and boating from your private dock. The low-rise coastal homes on stilts create a genuine Keys atmosphere where you can spot tropical birds and enjoy breathtaking sunset views.
You'll need to drive to nearby Cudjoe Key or Summerland Key for dining options featuring fresh seafood and Caribbean flavors. Vacation rental homes with waterfront views dominate accommodation choices. The neighborhood's layout prioritizes privacy and seclusion, making it ideal for travelers seeking the authentic Florida Keys lifestyle.
Sugarloaf Shores delivers waterfront paradise without the tourist crowds. Private canals weave between stilted homes where you can launch kayaks right from your rental's backyard dock. The crystal-clear backcountry waters beckon with world-class fishing, while gentle waves provide perfect spots for swimming and snorkeling.
Dining and shopping require a short drive, as this peaceful residential enclave focuses on natural beauty rather than commercial offerings. Most visitors stay in spacious vacation homes with private pools and boat docks. A rental car is essential for exploring the rest of the Florida Keys from this secluded waterfront haven.
Cudjoe Gardens offers a slice of authentic Florida Keys living with canal-front homes where you can park your boat right out back. This peaceful residential retreat lets you escape the crowds while still having easy access to the surrounding waters. Wildlife enthusiasts will spot herons stalking the shallows and fish jumping at sunrise while the gentle sound of water lapping against docks creates your vacation soundtrack.
Nearby restaurants in Summerland Key and Cudjoe Key serve up fresh seafood just a short drive away. Most homes feature private pools, boat docks, and tropical landscaping, all designed for relaxation and water activities. A rental car is essential for exploring the area, as this quiet community focuses on waterfront living rather than tourist amenities.
Breezeswept Beach Estates is a slice of Florida Keys paradise where private docks and waterfront homes replace tourist traps. You'll spend your days exploring crystal-clear waters, spotting marine life while kayaking, or casting a line into the Gulf. The surrounding Newfound Harbor Keys and nearby islands offer perfect day-trip adventures when you're ready to venture beyond your peaceful retreat.
Vacation rentals with tropical landscaping and breezy porches make up the accommodation options here. You'll need a car to reach restaurants on Ramrod Key or stock up on groceries for cooking. The quiet streets and gentle waves create the perfect soundtrack for stargazing and disconnecting from the everyday hustle.
Whether you want to collect beach glass or watch the sunset, Sugarloaf Beach is a spot you might want to check out, located 8.1 mi (13 km) from central Summerland Key. Catch the sunset by the shore at Florida Keys Beaches, just a short walk away.
Listen to the relaxing sound of the water and take some great vacation pics at Upper Sugarloaf Sound located 6.3 mi (10.2 km) from central Summerland Key.
This was great place to stay and was in a great location. Every thing was in walking distance and was only about 100 yards off Duval Street yet on the hotel property the gardens made you feel like you were in the middle of nowhere. I would highly recommend this place and we stay there next time I am back in Key West.
Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...
The room was clean and neat, everyone is very friendly and helpful. So glad we booked this place last minute. The best time we've ever had in Key west. You will not get anything more authentic than this place. Loved it!
Upon our arrival, the sight of 2 iguanas on the lounging on the bridge by the pristine water at the back of the property had my entire family out of the minivan at lightning speed. They followed one, which lead them to trees full of these beautiful lizards. The front desk personnel, a very amiable gentleman, was very friendly and welcoming. Our room was in the middle of the 2nd floor, and had a fantastic view of the bay. And yes, there were more iguanas looking at us from the first floor, some...
Rooms were right on the water with great views, property had some nice amenities and the boat ramp and slips were exactly what I needed. Annette at the front desk was super friendly and knows the true meaning of Customer Service. Because of her, we will be back for sure and tell all our friends, this is the place to stay!
The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food.
It was very frustrating that during our cumulative total of eight days stay, seven nights, the housekeeping plan was to only clean our room one time and it was on the seventh night. When we asked about this three days in, they said OK we can probably fit in one cleaning for you midway through your stay but that will be the only one, if you desire any additional cleanings that will be $150 each. When they cleaned the room, I would hardly call it clean. That was a little bit frustrating. Beyond...
Absolutely loved our stay! We rented a two story, two bedroom villa that exceeded our expectations. Having a full kitchen and a washer and dryer for a nice treat on a family trip. The villa was very clean and the beds were so comfortable. The beach and swimming area were amazing. We were able to snorkel and see tropical fish! Can’t wait to come back for another stay!
The Douglas House served as a perfect home base while in Key West. The location allows for easy access to all Duval has to offer. Really enjoyed being able to hear the national anthem being played every morning at 8 from the Navy base..
Great for a relaxing weekend, quiet hotel not too far from the main tourist center. We love the shuttle service provided by the hotel and his driver Gerry who guided us in every short trips. The only advice to the hotel is to provide the housekeeping service everyday without being requested by the guest, we expected this service to be included since the hotel charged an extra 51.00 usd per night!
Loved the walkability to Everywhere! Sunsets were Great and Private! Beach access was a Plus!!!!! Bar and restaurant were very convenient! Enjoyed The Atmosphere Very Much!!!
